CN114956122A - Copper-based metal cyanamide compound catalyst and preparation method and application thereof - Google Patents

Copper-based metal cyanamide compound catalyst and preparation method and application thereof Download PDF

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CN114956122A
CN114956122A CN202210695579.2A CN202210695579A CN114956122A CN 114956122 A CN114956122 A CN 114956122A CN 202210695579 A CN202210695579 A CN 202210695579A CN 114956122 A CN114956122 A CN 114956122A
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copper
based metal
compound catalyst
cyanamide compound
metal cyanamide
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黄富强
郑耿锋
王家成
孔舒仪
吕希蒙
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Shanghai Institute of Ceramics of CAS
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Shanghai Institute of Ceramics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
    • C01C3/00—Cyanogen; Compounds thereof
    • C01C3/16—Cyanamide; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
    • C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
    • C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
    • C25B11/075—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/82—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by IR- or Raman-data
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency
    • Y02P20/133—Renewable energy sources, e.g. sunlight

Abstract

The invention discloses a copper-based metal cyanamide compound catalyst and a preparation method and application thereof. The catalyst can solve the problems of low yield and poor selectivity of preparing methanol by electrocatalysis of carbon dioxide reduction, and realizes the preparation of methanol with high yield and high selectivity.

Description

Copper-based metal cyanamide compound catalyst and preparation method and application thereof
Technical Field
The invention relates to the technical field of electrocatalysis, in particular to a copper-based metal cyanamide compound catalyst and a preparation method and application thereof.
Background
The increase in carbon dioxide content has a great impact on climate, such as global warming, rising sea level and more unstable weather patterns. In connection with the containment of atmospheric airElevation of medium carbon dioxide levels, electrocatalytic carbon dioxide reduction (CO) 2 RR) is a potential strategy that can convert intermittent energy sources into high energy chemicals. This can reduce the dependence on petroleum resources, reduce atmospheric pollution, and artificially complete the final step of the carbon cycle.
CO 2 RR reaction takes place at the cathode of the electrolytic cell, consuming only CO 2 And H 2 And O, the reaction condition is mild. But CO 2 RR reaction is accompanied by hydrogen evolution reaction, and CO is inhibited 2 The reduction proceeds, resulting in a decrease in the selectivity of the catalytic reaction. In addition to competing hydrogen evolution reactions leading to reduced selectivity, the current density and yield of the product are related. Therefore, most of the CO is currently available 2 Catalytic work focuses on high selectivity and high current density in order to realize industrial applications.
Renewable electrically driven electrochemical CO 2 The reduction reaction is a promising reaction because it has the effect of converting CO 2 The ability to convert to methanol, theoretically with zero net life cycle emissions. However, according to recent evaluation of carbon emission, CO is a key index for measuring practical application prospect of electrocatalytic technology 2 Conversion to CH 3 The production efficiency of OH is still generally low. To improve conversion efficiency, several established strategies have been employed, including monatomic catalysts (SACs), specialty chalcogenides, and molecular catalysts. For example, monatomic catalysts can inhibit coupling reactions and provide C-1 selectivity, which may provide a higher probability for methanol, depending on the prevailing mechanisms. Inspired by the above, the group of new teaching questions has recently developed a load type Cu-SAC and obtained the highest CH at present 3 OH yield (706.8. mu. mol s) –1 m –2 ). On the other hand, electronic state regulation is also widely used (e.g. special chalcogenides, alloys, etc.) because the binding capacity of OH/O radicals and carbon species changes, possibly leading to thermodynamic advantages of the methanol pathway. In this regard, the group of kornbuch academy subjects achieved extremely high Faradaic Efficiency (FE) of 77.6% for methanol using copper selenide catalyst, but the production efficiency was still insufficient (556.3 μmol)s -1 m -2 ). Overall, most strategies to date have poor reactivity (<100mA cm -2 ) Or low selectivity to methanol (<10%), so there is still a need to develop new catalysts.
Disclosure of Invention
Aiming at the problems, the invention provides a copper-based metal cyanamide compound catalyst, and a preparation method and application thereof, wherein the catalyst can solve the problems of low yield and poor selectivity of preparing methanol by electrocatalysis of carbon dioxide reduction, and can realize high-yield and high-selectivity preparation of methanol.
In a first aspect, the present invention provides a copper-based metal cyanamide compound catalyst. The chemical structural formula of the copper-based metal cyanamide compound catalyst is Cu 2 NCN。
Preferably, the copper-based metal cyanamide compound catalyst exists in a bond type [ N ═ C ═ N ═ C-] 2- And/or bond type [ N-C.ident.N ≡ N-] 2- 。
Preferably, the preparation method comprises the following steps: dissolving a copper source in water to form a copper source water solution, and adjusting the copper source water solution to an alkaline solution with the pH value of 8-14 by adopting a pH regulator; adding cyanamide into the alkaline solution, and uniformly stirring to obtain a mixed solution; adding a reducing agent into the mixed solution, reacting at room temperature until precipitates are separated out, and collecting reaction products to obtain the copper-based metal cyanamide compound catalyst Cu 2 NCN。
In a second aspect, the present invention provides a copper-based metal cyanamide compound catalyst. The chemical structural formula of the copper-based metal cyanamide compound catalyst is CuNCN.
Preferably, the preparation method comprises the following steps: dissolving a copper source in water to form a copper source water solution, and adjusting the copper source water solution to an alkaline solution with the pH value of 8-14 by adopting a pH regulator; adding cyanamide into the alkaline solution, uniformly stirring, reacting for a period of time, and collecting a reaction product to obtain a copper-based metal cyanamide compound catalyst CuNCN.
Preferably, the molar ratio of the copper source to the cyanamide is 1: (1 to 100), preferably 1: (2-50).
Preferably, the molar ratio of the copper source to the hydroxide ions of the alkaline solution is 1: (0.1 to 50), preferably 1: (1-3).
Preferably, the molar ratio of the reducing agent to the cyanamide is 1: (1 to 100), preferably 1: (2-50).
In a third aspect, the present invention provides a copper-based metal cyanamide compound catalyst Cu 2 Use of NCN for electrocatalytic carbon dioxide reduction.
In a fourth aspect, the invention provides an application of a copper-based metal cyanamide compound catalyst CuNCN in electrocatalytic carbon dioxide reduction.
Drawings
FIG. 1 is a schematic representation of example 1 for electrocatalysis of CO 2 Reduced Cu 2 XRD pattern of NCN catalyst;
FIG. 2 is a schematic representation of example 1 for electrocatalysis of CO 2 Reduced Cu 2 An Infrared (IR) spectrum of the NCN catalyst;
FIG. 3 is a schematic representation of example 1 for electrocatalysis of CO 2 Reduced Cu 2 Methanol selectivity profile for NCN catalyst; the left is the H cell, the right is the MEA (Membrane electrode);
FIG. 4 is a schematic representation of example 1 for electrocatalysis of CO 2 Reduced Cu 2 Current density plot of NCN catalyst in MEA.
Detailed Description
The present invention is further illustrated by the following examples, which are to be understood as merely illustrative of, and not restrictive on, the present invention. Unless otherwise specified, each percentage means a mass percentage.
The invention discloses a copper-based metal cyanamide compound catalyst. The chemical structural formula of the copper-based metal cyanamide compound catalyst is Cu x And (3) NCN. When x is 1, the chemical structural formula of the copper-based metal cyanamide compound catalyst is CuNCN. The invention discloses the application of a copper-based metal cyanamide compound catalyst CuNCN in electrocatalysis of carbon dioxide reduction for the first time. When x is 2, the chemical structural formula of the copper-based metal cyanamide compound catalyst is Cu 2 And (3) NCN. In this case, the copper-based metal cyanamide compound catalyst has a bond type [ N ═ C ═ N-] 2- And/or bond type [ N-C.ident.N ≡ N-] 2- . The invention also provides the first proposal of copper-based metal cyanamideCompound catalyst Cu 2 NCN and determining its crystal structure.
The following exemplifies a method for preparing the copper-based metal cyanamide compound catalyst of the present invention.
The copper source is dissolved in water to form an aqueous copper source solution. The copper source serves to introduce copper ions. The copper source may be copper halide, copper sulfate, copper nitrate, etc. By way of example, the copper halide includes, but is not limited to, at least one of cupric chloride, cuprous chloride, cupric bromide, cuprous bromide. Likewise, the copper nitrate includes, but is not limited to, at least one of copper nitrate and cuprous nitrate.
And adjusting the copper source water solution to an alkaline solution with the pH value of 8-14 by adopting a pH regulator. The pH regulator includes but is not limited to at least one of ammonia, sodium hydroxide and potassium hydroxide. In some embodiments, the molar ratio of hydroxide to copper source to alkaline solution is 1: (0.1 to 50), preferably 1: (1-3). Within this range, Cu 2+ Does not excessively react to generate Cu (OH) 2 . In some embodiments, the pH of the alkaline solution is 8 to 10.
Adding cyanamide into the alkaline solution, and uniformly stirring to obtain a mixed solution. The function of the cyanamide is to provide the NCN required for the formation of the desired product 2- . The molar ratio of the copper source to the cyanamide is 1: (1 to 100), preferably 1: (2-50). Excess cyanamide can promote precipitation of the product.
If the copper-based metal cyanamide compound catalyst CuNCN is obtained, the mixture is dissolved and stirred uniformly and then reacted for a period of time until precipitate CuNCN is generated.
E.g. Cu in order to obtain a copper-based metal cyanamide compound catalyst 2 NCN, adding a reducing agent into the mixed solution, reacting at room temperature until the color of the solution changes, precipitating at the time, collecting a target product to obtain the copper-based metal cyanamide compound catalyst Cu 2 And (3) NCN. The reducing agent includes but is not limited to N 2 H 4 And/or Na 2 SO 3 。
The molar ratio of the reducing agent to the cyanamide is 1: (1 to 100), preferably 1: (2-50). Within this range, the reaction does not excessively occur to form the simple substance Cu.
In conclusion, the invention firstly provides the copper-based metal cyanamide compound catalysts CuNCN and Cu 2 Use of NCN for electrocatalysis of CO 2 Catalytic reaction of reduction and selective preparation of CH 3 And (5) OH. It is stated here that the copper-based metal cyanamide compound catalysts CuNCN and Cu can be used 2 NCN is used independently, or both may be used in combination. The mass ratio of the two may be varied as required. The copper-based metal cyanamide compound catalyst can be loaded on a catalyst for electrocatalysis of CO 2 Reduced CO gas diffusion electrodes, membrane electrodes, and the like 2 The above catalytic reaction is carried out in a reduction reactor. In addition, the invention also discloses a preparation method of the copper-based metal cyanamide compound catalyst, which has simple process and can realize batch preparation.
The present invention will be described in detail by way of examples. It is also to be understood that the following examples are illustrative of the present invention and are not to be construed as limiting the scope of the invention, and that certain insubstantial modifications and adaptations of the invention by those skilled in the art may be made in light of the above teachings. The specific process parameters and the like of the following examples are also only one example of suitable ranges, i.e., those skilled in the art can select the appropriate ranges through the description herein, and are not limited to the specific values exemplified below.
Example 1
Preparation for electrocatalytic CO 2 Reduced copper-based metal cyanamide compound catalyst Cu 2 And (3) NCN. 852mg of CuCl 2 Dissolved in 50mL of water to form a copper chloride solution. Adding 3mL of ammonia water with the mass fraction of 25% and 420mg of cyanamide into the copper chloride solution, and uniformly stirring to obtain a mixed solution. Adding 10mL of reducing agent hydrazine hydrate N into the mixed solution 2 H 4 Reacting at room temperature until the color of the solution changes, collecting the product, washing and drying to obtain the copper-based metal cyanamide compound catalyst Cu 2 NCN。
Copper-based metal cyanamide compound catalyst Cu prepared for example 1 2 The NCN was subjected to XRD and IR tests. FIG. 1 is a copper-based metal cyanamide compoundCatalyst Cu 2 Crystal structure diagram and XRD powder refinement of NCN. The solution was analyzed by 3D electron diffraction and confirmed to be a novel compound Cu 2 Crystal structure of NCN (CCDC No.: 2144240). As can be seen from fig. 1, the crystal structures are well matched. FIG. 2 is a copper-based metal cyanamide compound catalyst Cu 2 IR plot of NCN. Analysis of the IR results showed that two bond types were present simultaneously, i.e., [ N ═ C ═ N] 2- And [ N-C ≡ N ]] 2- And (5) structure.
The copper-based metal cyanamide compound catalyst Cu prepared in example 1 2 Electrocatalytic CO by NCN 2 And (5) reduction testing.
Cu 2 NCN as cathode catalyst, commercial IrO 2 the/Ni is used as an anode catalyst, and a cathode catalyst, an anode catalyst and an anion membrane coated on carbon paper are pressed together to obtain a Membrane Electrode Assembly (MEA). Assembling membrane electrode and metal plate assembly to obtain MEA reactor, introducing CO into the reactor 2 Electrocatalysis of CO with electrolyte 2 And (5) testing the reduction performance. And connecting the gas outlet of the reactor with a gas chromatograph, collecting the liquid product once at each reaction potential, and carrying out NMR (nuclear magnetic resonance) to test the components and the content of the liquid product. In the reaction process, an Autolab electrochemical workstation is adopted, and different potentials (2.8V, 3.0V, 3.2V, 3.4V and 3.6V) are selected for testing.
FIG. 3 is a schematic representation of a reactor for electrocatalytic CO 2 Reduced Cu 2 Methanol selectivity profile of NCN catalyst in membrane electrode electrolysis cell. It can be seen that in the membrane electrode, Cu 2 The selectivity of NCN catalyzing methanol reaches 68 percent, and the NCN catalyzing methanol has very excellent CO 2 The performance of methanol preparation by reduction.
FIG. 4 is a schematic representation of a reactor for electrocatalytic CO 2 Reduced Cu 2 Current density performance plot of NCN catalyst in membrane electrode cell. In the membrane electrode, Cu 2 The current density of NCN catalytic methanol reaches 92mA cm -2 Having very excellent CO 2 The performance of methanol preparation by reduction.
Example 2
Preparation for electrocatalytic CO 2 Reduced copper-based metal cyanamide compound catalyst Cu 2 And (3) NCN. 852mg of CuCl 2 DissolutionA copper chloride solution was formed in 50mL of water. Adding 3mL of ammonia water with the mass fraction of 25% and 420mg of cyanamide into the copper chloride solution, and uniformly stirring to obtain a mixed solution. Adding 10mL of reducing agent hydrazine hydrate N into the mixed solution 2 H 4 Reacting at room temperature until the color of the solution changes, collecting the product, washing and drying to obtain the copper-based metal cyanamide compound catalyst Cu 2 NCN。
The copper-based metal cyanamide compound catalyst Cu prepared in example 2 2 Electrocatalytic CO by NCN 2 And (5) reduction testing.
Mixing 10mg of Cu 2 NCN, 2mg carbon black, 50 mu L of binder nafion and 10mL of isopropanol or ethanol are mixed uniformly to prepare slurry. And dripping the slurry on the dried carbon felt. Working electrode in the electrolytic cell, Ag/AgCl reference electrode on one side of the H cell, and Pt counter electrode on the other side. The catalyst is electrolyzed and reacted in a closed H-shaped electrolytic cell under constant pressure. And connecting the gas outlet of the reactor with a gas chromatograph, collecting the liquid product once at each reaction potential, and carrying out NMR (nuclear magnetic resonance) to test the components and the content of the liquid product. In the reaction process, a Chenghua electrochemical workstation is adopted, and different potentials (-0.5V, -0.7V, -0.8V and-0.9V) are selected for testing.
Cu in an H-type cell, as shown in FIG. 3 2 The selectivity of methanol produced by NCN catalysis is 40-70%, and the selectivity of electrocatalytic methanol is excellent.
Example 3
Preparation for electrocatalytic CO 2 Reduced copper-based metal cyanamide compound catalyst Cu 2 And (3) NCN. 852mg of CuCl 2 Dissolved in 50mL of water to form a copper chloride solution. Adding 3mL of ammonia water with the mass fraction of 25% and 420mg of cyanamide into the copper chloride solution, and uniformly stirring to obtain a mixed solution. Adding 10mL of reducing agent hydrazine hydrate N into the mixed solution 2 H 4 Reacting at room temperature until the color of the solution changes, collecting the product, washing and drying to obtain the copper-based metal cyanamide compound catalyst Cu 2 NCN。
The copper-based metal cyanamide compound catalyst Cu prepared in example 3 2 Electrocatalytic CO by NCN 2 And (5) reduction testing.
Cu 2 NCN as cathode catalyst, commercial IrO 2 the/Ni is used as an anode catalyst, and a cathode catalyst, an anode catalyst and an anion membrane coated on carbon paper are assembled with a metal plate assembly and the like to obtain the gas diffusion electrode. Introducing CO into the gas end of the gas diffusion electrode 2 The liquid interface is communicated with electrolyte to carry out electrocatalysis on CO 2 And (5) testing the reduction performance. The gas outlet of the reactor was connected to a gas chromatograph and the liquid product was collected once at each reaction potential and subjected to NMR to test the composition and content of the liquid product. In the reaction process, a Chenghua electrochemical workstation is adopted, and different potentials (-0.5V, -0.7V, -0.8V and-0.9V) are selected for testing. In gas diffusion electrodes, Cu 2 The selectivity of methanol production by NCN catalysis is 50-70%, and the selectivity of electrocatalytic methanol is excellent.
Example 4
Preparation for electrocatalytic CO 2 Reduced copper-based metal cyanamide compound catalyst CuNCN. 852mg of CuCl 2 Dissolved in 50mL of water to form a copper chloride solution. Adding 3mL of 25% ammonia water and 420mg of cyanamide in parts by mass into the copper chloride solution, uniformly stirring, reacting for a period of time, and washing to obtain the copper-based metal cyanamide compound catalyst CuNCN. The copper-based metal cyanamide compound catalyst CuNCN prepared in example 4 is used for electrocatalysis of CO 2 And (5) reduction testing.
10mg of CuNCN, 2mg of carbon black, 50 mu L of binder nafion and 10mL of isopropanol or ethanol are mixed uniformly to prepare slurry. And dripping the slurry on the dried carbon felt. In the electrolytic cell, a working electrode and an Ag/AgCl reference electrode are arranged on one side of the H cell, and a Pt counter electrode is arranged on the other side. In a closed H-type electrolytic cell, the catalyst is subjected to electrolytic reaction under constant pressure. And connecting the gas outlet of the reactor with a gas chromatograph, collecting the liquid product once at each reaction potential, and carrying out NMR (nuclear magnetic resonance) to test the components and the content of the liquid product. In the reaction process, a Chenghua electrochemical workstation is adopted, and different potentials (-0.5V, -0.7V, -0.8V and-0.9V) are selected for testing. In an H-type electrolytic cell, the selectivity of CuNCN catalysis for methanol production is 20%, and certain electrocatalytic methanol selectivity is achieved.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. The copper-based metal cyanamide compound catalyst is characterized in that the chemical structural formula of the copper-based metal cyanamide compound catalyst is Cu 2 NCN。
2. Copper-based metal cyanamide compound catalyst according to claim 1, characterized in that the copper-based metal cyanamide compound catalyst exists in a bond type [ N = C = N { ]] 2- And/or bond type [ N-C.ident.N ≡ N-] 2- 。
3. The production method of a copper-based metal cyanamide compound catalyst according to claim 1 or 2, characterized by comprising the steps of: dissolving a copper source in water to form a copper source water solution, and adjusting the copper source water solution to an alkaline solution with the pH value of 8-14 by adopting a pH regulator; adding cyanamide into the alkaline solution, and uniformly stirring to obtain a mixed solution; adding a reducing agent into the mixed solution, reacting at room temperature until precipitates are separated out, and collecting reaction products to obtain the copper-based metal cyanamide compound catalyst Cu 2 NCN。
4. The copper-based metal cyanamide compound catalyst is characterized in that the chemical structural formula of the copper-based metal cyanamide compound catalyst is CuNCN.
5. The production method of a copper-based metal cyanamide compound catalyst according to claim 4, characterized by comprising the steps of: dissolving a copper source in water to form a copper source water solution, and adjusting the copper source water solution to an alkaline solution with the pH value of 8-14 by adopting a pH regulator; adding cyanamide into the alkaline solution, uniformly stirring, reacting for a period of time, and collecting a reaction product to obtain a copper-based metal cyanamide compound catalyst CuNCN.
6. The production method according to claim 3 or 5, wherein the molar ratio of the copper source to the cyanamide is 1: (1 to 100), preferably 1: (2-50).
7. The production method according to claim 3 or 5, wherein the molar ratio of the copper source to the hydroxide ions of the alkaline solution is 1: (0.1 to 50), preferably 1: (1-3).
8. The method according to claim 3, wherein the molar ratio of the reducing agent to the cyanamide is 1: (1 to 100), preferably 1: (2-50).
9. The copper-based metal cyanamide compound catalyst Cu of claim 1 2 Use of NCN for electrocatalytic carbon dioxide reduction.
10. The use of the copper-based metal cyanamide compound catalyst CuNCN of claim 4 in electrocatalytic carbon dioxide reduction.
CN202210695579.2A 2022-06-20 2022-06-20 Copper-based metal cyanamide compound catalyst and preparation method and application thereof Pending CN114956122A (en)

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US3410658A (en) * 1962-08-09 1968-11-12 Du Pont Cyanogen azide, compositions containing this compound, and the preparation of the same from cyanogen halides and metal azides
CN109817935A (en) * 2019-01-31 2019-05-28 陕西科技大学 A kind of compound iron carbodiimide cell negative electrode material and preparation method thereof
CN110102300A (en) * 2019-06-05 2019-08-09 中北大学 Monatomic catalyst of a kind of flexibility carbon-based supports carried metal and its preparation method and application

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Title
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